Enzymatic synthesis of l-menthyl esters in organic solvent-free system
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l-Menthol has been widely used as a food additive and an ingredient of cosmetics, and it is esterified to moderate the strong flavor. We attempted esterification of l-menthol with long-chain unsaturated fatty acid in an organic solvent-free enzymatic system. Commercially available lipases were screened, and Candida rugosa lipase was selected as a catalyst. Several factors affecting the esterification were investigated, and the reaction conditions were determined as follows: A reaction mixture of l-menthol/fatty acid (1:3, mol/mol), 30% water, and 700 units of the lipase per gram of reaction mixture was incubated at 30°C with stirring. After 24 h under these conditions, the esterification extents of l-menthol with oleic, linoleic, and α-linolenic acids reached 96, 88, and 95%, respectively. The structure of the esterified product was confirmed by mass, infrared, and nuclear magnetic resonance spectroscopies. Bacause Candida lipase acted strongly on l-menthol and very weakly on d-menthol, dl-menthol was esterified with oleic acid under the same conditions. The reaction showed high enantioselectivity; the enantiomeric ratio (E) was 31, and enantiomeric excess (ee) of l-menthyl oleate reached 88% after 32 h.
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- Enzymatic synthesis of l-menthyl esters in organic solvent-free system
Journal of the American Oil Chemists’ Society
Volume 76, Issue 10 , pp 1139-1142
- Cover Date
- Print ISSN
- Online ISSN
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- Candida rugosa
- fatty acids
- optical resolution
- Industry Sectors
- Author Affiliations
- 1. Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, 536-8553, Osaka, Japan
- 2. Department of Applied Chemistry, Osaka Institute of Technology, 535-8585, Osaka, Japan
- 3. Maruha Corp., 300-4295, Ibaraki, Japan